Trimethyl borate → [4-(Nonyloxy)phenyl]boronic acid

HRID 1459096Notes

Reaction equation

HRID 1459096 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1.C([Li])CCC.[B:23](OC)([O:26]C)[O:24]C.C(OC1C=CC(B(O)O)=CC=1)CCCCCCC>C1COCC1>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([B:23]([OH:26])[OH:24])=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 14640447HCID 14640447, compoundHCID 178418339Butyllithium

Product 1

HCID 4197997[4-(Nonyloxy)phenyl]boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Quantities: compound 27 (14.70 g, 0.066 mol) in anhydrous THF (140 ml), n-butyllithium (30 ml, 2.5M in hexane, 0.075 mol), trimethyl borate (13.72 g, 0.132 mol) in anhydrous THF (50 ml). The experimental procedure was as described for the preparation of compound 33.

Sources & evidence

ORD record
ord-fabcc536a60946ac996a141221922789
Source dataset
uspto-grants-1998_12
Patent number
US05853613

Reaction notes

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